Cyclades · 14 days
Cyclades in 14 days
Two weeks lets this route cover seven islands rather than skim four, moving from the working port town of Syros through the pilgrimage island of Tinos and the beach-club energy of Mykonos before slowing down on Naxos, Milos, and finally Santorini. It suits travelers who want real range across the archipelago and do not mind a ferry day every two or three stops.
Day by day
- Day 1 Athens (Piraeus)
Athens opens the trip with the Acropolis and an evening in Plaka before the fast ferry to Syros, a 2h 15m crossing that runs year-round.
Athens (Piraeus) → Syros · 2h 15m · from €52 - Day 2–3 Syros
Syros is a working port city rather than a village: Ermoupoli's neoclassical waterfront and the hilltop quarter of Ano Syros fill the two nights before a 30-minute hop to Tinos.
Syros → Tinos · 30m · from €26 - Day 4–5 Tinos
Tinos centers on the pilgrimage church of Panagia Evangelistria, but the marble-carved villages and stone dovecotes inland reward a rental car; the boat to Mykonos is a short 20-minute run.
Tinos → Mykonos · 20m · from €25 - Day 6–7 Mykonos
Mykonos brings Chora, Little Venice, the windmills, and a day trip out to Delos before the 45-minute ferry to Naxos.
Mykonos → Naxos · 45m · from €39 - Day 8–9 Naxos
Naxos pairs the Kastro fortress with a drive through Tragaea and up toward Mount Zas, the tallest peak in the Cyclades, before the onward connection to Milos.
- Day 10–11 Milos
There is no direct boat from Naxos to Milos, so this leg usually means a change of ferry — check the day's schedule when booking. Once there, Milos delivers the Sarakiniko moonscape, a boat trip around the Kleftiko sea caves, and the pastel-colored village of Plaka.
Milos → Santorini · 1h 50m · from €58 - Day 12–14 Santorini
Santorini closes the trip with three nights for the caldera walk from Fira to Oia, a wine tasting, and a final look at the volcano from the water; the fast ferry from Milos takes about 1h 50m.
Times, prices and frequencies are indicative and change by season and operator. Always confirm the live timetable before you book.